Lenny's Newsletter this week surfaces five practitioner debates from its members-only Slack: how to stay visible to a client during a stalled pilot, which discovery tool pairs with Linear for roadmap work, where AI automation actually breaks down, and whether a Techstars cohort still returns its cost in 2024.
The pilot purgatory thread is the lead item, which signals it drew the most signal from the community. Enterprise deals dying in silence between signed pilot and renewal decision is a concrete, recurring failure mode. The specific tactics practitioners recommend for re-entry are behind the paywall.
The AI automation limits thread is the one worth reading in full. Practitioners drawing lines around what AI can and cannot own in a product workflow is more durable than any tool review. The Techstars debate adds a second high-stakes question with real dollar implications for anyone considering an accelerator in the current funding climate.
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